Martha Stewart

By Kevin Mazur/WireImage/Getty Images.

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Twenty years ago, at the steepest grade of her remarkable ascent, Martha Stewart had already written dozens of books, was running a namesake lifestyle magazine, and hosting a syndicated weekly TV show with 5 million viewers (big numbers even in those days). New York magazine put her on its cover, proclaiming her “the definitive American woman of our time” and, better yet, “a living trademark.” “She’s a combination of Amazonian strength, Olympian omnipotence, and Emersonian self-reliance,” Stewart’s friend, postmodern novelist Mark Leyner, gushed to the magazine. “Soon she’s going to branch into nuclear weaponry, cold fusion, and voodoo.” And insider trading, as fate would have it.

Just as remarkable as her rise was Stewart’s meteoric descent. Convicted on charges related to insider trading for trying to avoid a mere $45,673 stock loss—roughly one-fifteen-thousandth of her net worth at the time—she spent five months in West Virginia’s Federal Prison Camp, Alderson (where she earned the nickname “M. Diddy”). On the surface it seems an open-and-shut case of penny-wise and pound-foolish, but it revealed a darker and more complicated side to America’s homemaking queen.

Sure, she’s been the butt of late-night jokes (David Letterman: “It was gorgeous here today! Just beautiful. It was so nice that Martha Stewart was doing her insider trading outside”); but her rise from the ashes is very nearly realized, and she’s finally able to laugh about it. She’s also learned how to give as good as she gets, killing it at Justin Bieber’s Comedy Central roast last year, giving the J.Beebs “tips to use when he inevitably ends up in prison.”